JP2003523475A - フォトクロミックポリウレタンコーティングおよびこのコーティングを有する物品 - Google Patents
フォトクロミックポリウレタンコーティングおよびこのコーティングを有する物品Info
- Publication number
- JP2003523475A JP2003523475A JP2001561112A JP2001561112A JP2003523475A JP 2003523475 A JP2003523475 A JP 2003523475A JP 2001561112 A JP2001561112 A JP 2001561112A JP 2001561112 A JP2001561112 A JP 2001561112A JP 2003523475 A JP2003523475 A JP 2003523475A
- Authority
- JP
- Japan
- Prior art keywords
- photochromic
- polyols
- article
- poly
- monomer
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
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- 238000000576 coating method Methods 0.000 title abstract description 68
- 239000011248 coating agent Substances 0.000 title abstract description 57
- 229920005862 polyol Polymers 0.000 claims abstract description 153
- 150000003077 polyols Chemical class 0.000 claims abstract description 147
- 239000004417 polycarbonate Substances 0.000 claims abstract description 50
- 229920000515 polycarbonate Polymers 0.000 claims abstract description 50
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 39
- 238000012360 testing method Methods 0.000 claims abstract description 26
- 239000000203 mixture Substances 0.000 claims description 91
- 239000000178 monomer Substances 0.000 claims description 70
- 239000000463 material Substances 0.000 claims description 61
- 239000012948 isocyanate Substances 0.000 claims description 56
- 150000002513 isocyanates Chemical class 0.000 claims description 46
- -1 poly (oxytetramethylene) Polymers 0.000 claims description 43
- 150000001875 compounds Chemical class 0.000 claims description 39
- 238000006243 chemical reaction Methods 0.000 claims description 26
- 230000003287 optical effect Effects 0.000 claims description 25
- 239000004814 polyurethane Substances 0.000 claims description 25
- 229920002635 polyurethane Polymers 0.000 claims description 25
- 229920000642 polymer Polymers 0.000 claims description 24
- 239000000758 substrate Substances 0.000 claims description 23
- IISBACLAFKSPIT-UHFFFAOYSA-N Bisphenol A Natural products C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 21
- 229920001577 copolymer Polymers 0.000 claims description 21
- 125000003003 spiro group Chemical group 0.000 claims description 20
- 150000002009 diols Chemical class 0.000 claims description 18
- 239000000126 substance Substances 0.000 claims description 17
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 13
- 229920005906 polyester polyol Polymers 0.000 claims description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 12
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 claims description 12
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 claims description 12
- 229920000570 polyether Polymers 0.000 claims description 12
- 125000001931 aliphatic group Chemical group 0.000 claims description 10
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 9
- 239000007787 solid Substances 0.000 claims description 9
- 229920001169 thermoplastic Polymers 0.000 claims description 9
- 239000004416 thermosoftening plastic Substances 0.000 claims description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 8
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 8
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 8
- XFSAZBKSWGOXRH-UHFFFAOYSA-N 2-(2-carbonochloridoyloxyethoxy)ethyl carbonochloridate Chemical compound ClC(=O)OCCOCCOC(Cl)=O XFSAZBKSWGOXRH-UHFFFAOYSA-N 0.000 claims description 7
- JHQVCQDWGSXTFE-UHFFFAOYSA-N 2-(2-prop-2-enoxycarbonyloxyethoxy)ethyl prop-2-enyl carbonate Chemical compound C=CCOC(=O)OCCOCCOC(=O)OCC=C JHQVCQDWGSXTFE-UHFFFAOYSA-N 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 7
- 239000004593 Epoxy Substances 0.000 claims description 7
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 claims description 7
- JKJWYKGYGWOAHT-UHFFFAOYSA-N bis(prop-2-enyl) carbonate Chemical compound C=CCOC(=O)OCC=C JKJWYKGYGWOAHT-UHFFFAOYSA-N 0.000 claims description 7
- 239000011521 glass Substances 0.000 claims description 7
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 claims description 7
- 229920001223 polyethylene glycol Polymers 0.000 claims description 7
- 229920001451 polypropylene glycol Polymers 0.000 claims description 7
- XFCMNSHQOZQILR-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOC(=O)C(C)=C XFCMNSHQOZQILR-UHFFFAOYSA-N 0.000 claims description 6
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 6
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 6
- 230000001681 protective effect Effects 0.000 claims description 6
- 229920002554 vinyl polymer Polymers 0.000 claims description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 5
- 239000012975 dibutyltin dilaurate Substances 0.000 claims description 5
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Chemical compound CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 claims description 5
- WHIVNJATOVLWBW-UHFFFAOYSA-N n-butan-2-ylidenehydroxylamine Chemical compound CCC(C)=NO WHIVNJATOVLWBW-UHFFFAOYSA-N 0.000 claims description 5
- 229920000620 organic polymer Polymers 0.000 claims description 5
- 239000002861 polymer material Substances 0.000 claims description 5
- 239000004926 polymethyl methacrylate Substances 0.000 claims description 5
- HIACAHMKXQESOV-UHFFFAOYSA-N 1,2-bis(prop-1-en-2-yl)benzene Chemical compound CC(=C)C1=CC=CC=C1C(C)=C HIACAHMKXQESOV-UHFFFAOYSA-N 0.000 claims description 4
- ZTNJGMFHJYGMDR-UHFFFAOYSA-N 1,2-diisocyanatoethane Chemical compound O=C=NCCN=C=O ZTNJGMFHJYGMDR-UHFFFAOYSA-N 0.000 claims description 4
- SKESERDUDQOXKM-UHFFFAOYSA-N 2-methylprop-2-enoic acid;phenol Chemical class CC(=C)C(O)=O.CC(=C)C(O)=O.OC1=CC=CC=C1 SKESERDUDQOXKM-UHFFFAOYSA-N 0.000 claims description 4
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 4
- 239000004793 Polystyrene Substances 0.000 claims description 4
- QUZSUMLPWDHKCJ-UHFFFAOYSA-N bisphenol A dimethacrylate Chemical class C1=CC(OC(=O)C(=C)C)=CC=C1C(C)(C)C1=CC=C(OC(=O)C(C)=C)C=C1 QUZSUMLPWDHKCJ-UHFFFAOYSA-N 0.000 claims description 4
- 229940043279 diisopropylamine Drugs 0.000 claims description 4
- 230000001747 exhibiting effect Effects 0.000 claims description 4
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical group O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 4
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims description 4
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 claims description 4
- 229920002223 polystyrene Polymers 0.000 claims description 4
- 229920002578 polythiourethane polymer Polymers 0.000 claims description 4
- 229920002689 polyvinyl acetate Polymers 0.000 claims description 4
- 239000011118 polyvinyl acetate Substances 0.000 claims description 4
- 235000019422 polyvinyl alcohol Nutrition 0.000 claims description 4
- 150000005846 sugar alcohols Polymers 0.000 claims description 4
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 claims description 4
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 claims description 3
- GTELLNMUWNJXMQ-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical class OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.CCC(CO)(CO)CO GTELLNMUWNJXMQ-UHFFFAOYSA-N 0.000 claims description 3
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 claims description 3
- 239000002202 Polyethylene glycol Substances 0.000 claims description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 3
- 125000005907 alkyl ester group Chemical group 0.000 claims description 3
- 229920002301 cellulose acetate Polymers 0.000 claims description 3
- FOTKYAAJKYLFFN-UHFFFAOYSA-N decane-1,10-diol Chemical compound OCCCCCCCCCCO FOTKYAAJKYLFFN-UHFFFAOYSA-N 0.000 claims description 3
- SXCBDZAEHILGLM-UHFFFAOYSA-N heptane-1,7-diol Chemical compound OCCCCCCCO SXCBDZAEHILGLM-UHFFFAOYSA-N 0.000 claims description 3
- 150000001282 organosilanes Chemical group 0.000 claims description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 3
- 238000011056 performance test Methods 0.000 claims description 3
- 229920003229 poly(methyl methacrylate) Polymers 0.000 claims description 3
- 229920000728 polyester Polymers 0.000 claims description 3
- 229920000915 polyvinyl chloride Polymers 0.000 claims description 3
- 239000004800 polyvinyl chloride Substances 0.000 claims description 3
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 claims description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 2
- ITHGKFNFXCDUDC-UHFFFAOYSA-N 2,3-dihydro-1h-benzo[g]indole;2h-pyrido[2,3-h][1,2]benzoxazine Chemical compound C1=CC=CC2=C(NCC3)C3=CC=C21.C1=CC2=NC=CC=C2C2=C1C=CNO2 ITHGKFNFXCDUDC-UHFFFAOYSA-N 0.000 claims description 2
- WCQAZRJBAWCCMZ-UHFFFAOYSA-N 2,3-dihydro-1h-indole;2h-pyran Chemical compound C1OC=CC=C1.C1=CC=C2NCCC2=C1 WCQAZRJBAWCCMZ-UHFFFAOYSA-N 0.000 claims description 2
- UJKRMSUGENCHEY-UHFFFAOYSA-N 2,3-dihydro-1h-indole;2h-pyrano[3,2-b]quinoline Chemical compound C1=CC=C2NCCC2=C1.C1=CC=C2N=C(C=CCO3)C3=CC2=C1 UJKRMSUGENCHEY-UHFFFAOYSA-N 0.000 claims description 2
- RFPBBTGDNJHSRB-UHFFFAOYSA-N 2,3-dihydro-1h-indole;2h-pyrido[2,3-h][1,2]benzoxazine Chemical compound C1=CC=C2NCCC2=C1.C1=CC2=NC=CC=C2C2=C1C=CNO2 RFPBBTGDNJHSRB-UHFFFAOYSA-N 0.000 claims description 2
- VFUGUWZYXGNQHR-UHFFFAOYSA-N 2h-1,2-benzoxazine;2,3-dihydro-1h-indole Chemical compound C1=CC=C2NCCC2=C1.C1=CC=C2C=CNOC2=C1 VFUGUWZYXGNQHR-UHFFFAOYSA-N 0.000 claims description 2
- ZLLLODBXLDFWER-UHFFFAOYSA-N 2h-chromene;2,3-dihydro-1h-indole Chemical compound C1=CC=C2NCCC2=C1.C1=CC=C2C=CCOC2=C1 ZLLLODBXLDFWER-UHFFFAOYSA-N 0.000 claims description 2
- ITPCCQOGYMDBHK-UHFFFAOYSA-N 3h-benzo[f][1,2]benzoxazine;2,3-dihydro-1h-indole Chemical compound C1=CC=C2NCCC2=C1.C1=CC=CC2=C(C=CNO3)C3=CC=C21 ITPCCQOGYMDBHK-UHFFFAOYSA-N 0.000 claims description 2
- VCMLCMCXCRBSQO-UHFFFAOYSA-N 3h-benzo[f]chromene Chemical compound C1=CC=CC2=C(C=CCO3)C3=CC=C21 VCMLCMCXCRBSQO-UHFFFAOYSA-N 0.000 claims description 2
- HEDFZCGDROAIPW-UHFFFAOYSA-N 3h-benzo[f]chromene;2,3-dihydro-1h-benzo[g]indole Chemical compound C1=CC=CC2=C(NCC3)C3=CC=C21.C1=CC=CC2=C(C=CCO3)C3=CC=C21 HEDFZCGDROAIPW-UHFFFAOYSA-N 0.000 claims description 2
- VQEXVGHCYCLGMW-UHFFFAOYSA-N 3h-benzo[f]chromene;2,3-dihydro-1h-indole Chemical compound C1=CC=C2NCCC2=C1.C1=CC=CC2=C(C=CCO3)C3=CC=C21 VQEXVGHCYCLGMW-UHFFFAOYSA-N 0.000 claims description 2
- KYNSBQPICQTCGU-UHFFFAOYSA-N Benzopyrane Chemical compound C1=CC=C2C=CCOC2=C1 KYNSBQPICQTCGU-UHFFFAOYSA-N 0.000 claims description 2
- OAICMCPFPDINEH-UHFFFAOYSA-N C1=CNOC2=C1C1=CC=CC=C1C=C2.N2CCC1=CC=C3C(=C21)C=CC=C3 Chemical compound C1=CNOC2=C1C1=CC=CC=C1C=C2.N2CCC1=CC=C3C(=C21)C=CC=C3 OAICMCPFPDINEH-UHFFFAOYSA-N 0.000 claims description 2
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- 229920002284 Cellulose triacetate Polymers 0.000 claims description 2
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- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 claims description 2
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- 238000004061 bleaching Methods 0.000 claims description 2
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- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 claims description 2
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- 125000005702 oxyalkylene group Chemical group 0.000 claims description 2
- 239000000123 paper Substances 0.000 claims description 2
- QIWKUEJZZCOPFV-UHFFFAOYSA-N phenyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=CC=C1 QIWKUEJZZCOPFV-UHFFFAOYSA-N 0.000 claims description 2
- 229920003251 poly(α-methylstyrene) Polymers 0.000 claims description 2
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- 239000004632 polycaprolactone Substances 0.000 claims description 2
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- BIXBNZDQRGVVJE-UHFFFAOYSA-N 2h-naphtho[2,1-f]chromene Chemical compound C1=CC=C2C3=CC=C4OCC=CC4=C3C=CC2=C1 BIXBNZDQRGVVJE-UHFFFAOYSA-N 0.000 claims 1
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- 239000010410 layer Substances 0.000 description 6
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- 229920003023 plastic Polymers 0.000 description 6
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- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
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- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
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- VLJQDHDVZJXNQL-UHFFFAOYSA-N 4-methyl-n-(oxomethylidene)benzenesulfonamide Chemical compound CC1=CC=C(S(=O)(=O)N=C=O)C=C1 VLJQDHDVZJXNQL-UHFFFAOYSA-N 0.000 description 4
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 4
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- XLAIWHIOIFKLEO-OWOJBTEDSA-N trans-stilbene-4,4'-diol Chemical compound C1=CC(O)=CC=C1\C=C\C1=CC=C(O)C=C1 XLAIWHIOIFKLEO-OWOJBTEDSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 238000011179 visual inspection Methods 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
- G03C1/685—Compositions containing spiro-condensed pyran compounds or derivatives thereof, as photosensitive substances
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/44—Polycarbonates
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
- Y10T428/31598—Next to silicon-containing [silicone, cement, etc.] layer
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Physics & Mathematics (AREA)
- Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polyurethanes Or Polyureas (AREA)
- Paints Or Removers (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US17809500P | 2000-01-26 | 2000-01-26 | |
| US60/178,095 | 2000-01-26 | ||
| US09/755,147 US20020009599A1 (en) | 2000-01-26 | 2001-01-08 | Photochromic polyurethane coating and articles having such a coating |
| US09/755,147 | 2001-01-08 | ||
| PCT/US2001/002379 WO2001055269A1 (en) | 2000-01-26 | 2001-01-25 | Photochromic polyurethane coating and articles having such a coating |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JP2003523475A true JP2003523475A (ja) | 2003-08-05 |
Family
ID=26873963
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001561112A Pending JP2003523475A (ja) | 2000-01-26 | 2001-01-25 | フォトクロミックポリウレタンコーティングおよびこのコーティングを有する物品 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US20020009599A1 (es) |
| EP (1) | EP1263902A1 (es) |
| JP (1) | JP2003523475A (es) |
| AU (1) | AU4142601A (es) |
| BR (1) | BR0108110A (es) |
| CA (1) | CA2397969A1 (es) |
| MX (1) | MXPA02007285A (es) |
| WO (1) | WO2001055269A1 (es) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012516376A (ja) * | 2009-01-30 | 2012-07-19 | ザ・ボーイング・カンパニー | ハイブリッドコーティング及び関連の塗布方法 |
| WO2012141250A1 (ja) * | 2011-04-13 | 2012-10-18 | 株式会社トクヤマ | フォトクロミック組成物 |
| JP2014505116A (ja) * | 2010-11-23 | 2014-02-27 | トランジションズ オプティカル， インコーポレイテッド | 硬化性フォトクロミック組成物およびそれから調製される光学物品 |
| JP2016540239A (ja) * | 2013-10-11 | 2016-12-22 | トランジションズ オプティカル， インコーポレイテッド | 有機溶媒前処理およびフォトクロミックコーティングを使用するフォトクロミック光学物品を調製する方法 |
| WO2021172404A1 (ja) * | 2020-02-27 | 2021-09-02 | 株式会社トクヤマ | 光学物品用プライマー組成物、および積層体 |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001002449A2 (en) * | 1999-07-02 | 2001-01-11 | Ppg Industries Ohio, Inc. | Poly(meth)acrylic photochromic coating |
| FR2812646A1 (fr) * | 2000-08-04 | 2002-02-08 | Rhodia Chimie Sa | Composition polyisocyanate obtenue par polymerisation de monomeres isocyanates et composes polyisocyanates masques |
| FR2819800B1 (fr) * | 2001-01-25 | 2003-08-29 | Essilor Int | Procede d'incorporation d'un additif dans une couche mince formee sur un substrat et son application a l'optique ophtalmique |
| US7410691B2 (en) | 2001-12-27 | 2008-08-12 | Ppg Industries Ohio, Inc. | Photochromic optical article |
| US7108958B2 (en) * | 2002-07-31 | 2006-09-19 | Brewer Science Inc. | Photosensitive bottom anti-reflective coatings |
| US7259122B1 (en) * | 2004-08-30 | 2007-08-21 | John Lombardi | Chemically-resistant shelter coating |
| US7915197B2 (en) * | 2003-08-29 | 2011-03-29 | Lombardi John L | Pathogen-resistant coatings |
| AU2004270746B2 (en) | 2003-09-09 | 2010-12-02 | Insight Equity A.P.X., Lp | Photochromic polyurethane laminate |
| US7364835B2 (en) * | 2003-10-15 | 2008-04-29 | Brewer Science Inc. | Developer-soluble materials and methods of using the same in via-first dual damascene applications |
| US7261843B2 (en) * | 2004-03-04 | 2007-08-28 | Transitions Optical, Inc. | Photochromic optical article |
| US7189456B2 (en) | 2004-03-04 | 2007-03-13 | Transitions Optical, Inc. | Photochromic optical article |
| US20070207406A1 (en) * | 2004-04-29 | 2007-09-06 | Guerrero Douglas J | Anti-reflective coatings using vinyl ether crosslinkers |
| US20050255410A1 (en) * | 2004-04-29 | 2005-11-17 | Guerrero Douglas J | Anti-reflective coatings using vinyl ether crosslinkers |
| US7258437B2 (en) | 2005-09-07 | 2007-08-21 | Transitions Optical, Inc. | Photochromic multifocal optical article |
| SE0502284L (sv) * | 2005-10-14 | 2006-12-27 | Perstorp Specialty Chem Ab | Polyurethane elastomer |
| JP2007256173A (ja) * | 2006-03-24 | 2007-10-04 | Olympus Corp | 外観検査装置 |
| US7914974B2 (en) | 2006-08-18 | 2011-03-29 | Brewer Science Inc. | Anti-reflective imaging layer for multiple patterning process |
| KR100764108B1 (ko) | 2007-03-28 | 2007-10-05 | 구자은 | 렌즈 코팅 프라이머용 수분산 폴리우레탄 및 이의 제조방법 |
| US7998529B2 (en) * | 2007-10-10 | 2011-08-16 | Ppg Industries Ohio, Inc. | Methods for making polymeric substrates comprising a haze-free, self-healing coating and coated substrates made thereby |
| EP2245512B1 (en) | 2008-01-29 | 2019-09-11 | Brewer Science, Inc. | On-track process for patterning hardmask by multiple dark field exposures |
| US9640396B2 (en) | 2009-01-07 | 2017-05-02 | Brewer Science Inc. | Spin-on spacer materials for double- and triple-patterning lithography |
| DE102009005711A1 (de) * | 2009-01-22 | 2010-07-29 | Bayer Materialscience Ag | Polyurethanvergussmassen |
| US8815771B2 (en) | 2012-04-16 | 2014-08-26 | Ppg Industries Ohio, Inc. | Mechanochromic coating composition |
| US9081130B1 (en) | 2013-01-09 | 2015-07-14 | Insight Equity A.P.X., Lp | Photochromic polyurethane laminate |
| US9440419B2 (en) | 2013-03-15 | 2016-09-13 | Vision Ease, Lp | Photochromic polyurethane laminate |
| CN107922605B (zh) | 2015-09-03 | 2020-12-11 | 株式会社德山 | 聚轮烷及其制法以及含有该聚轮烷的光学用组合物 |
| CN109535888A (zh) * | 2018-10-25 | 2019-03-29 | 广州市科涵实业有限责任公司 | 一种单组分光致变色涂料及其制备方法 |
| CN112210099B (zh) * | 2020-10-12 | 2023-04-04 | 南京摩开科技有限公司 | 一种光致变色聚氨酯薄膜及其制备方法 |
| US11952492B2 (en) | 2020-11-20 | 2024-04-09 | Encapsys, Llc | Biodegradable, controlled release microcapsules |
| CN116178666A (zh) * | 2023-02-14 | 2023-05-30 | 华南理工大学 | 一种聚硅氧烷聚氨酯超分子弹性体及其制备方法和应用 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4101529A (en) * | 1976-02-04 | 1978-07-18 | Ppg Industries, Inc. | Hard, optically clear polyurethane articles |
| JPS63178193A (ja) * | 1987-01-20 | 1988-07-22 | Nippon Sheet Glass Co Ltd | フオトクロミツク性を有する被覆用組成物 |
| JPH08120223A (ja) * | 1994-10-25 | 1996-05-14 | Okamoto Ind Inc | 弾性成形型用の表面被覆剤 |
| FR2732019B1 (fr) * | 1995-03-24 | 1997-06-13 | Flamel Tech Sa | Spiropyrannes photochromiques, compositions et articles les contenant |
| CA2255381C (en) * | 1997-12-29 | 2008-09-16 | Bayer Corporation | Photochromic polyurethanes |
-
2001
- 2001-01-08 US US09/755,147 patent/US20020009599A1/en not_active Abandoned
- 2001-01-25 AU AU41426/01A patent/AU4142601A/en not_active Abandoned
- 2001-01-25 JP JP2001561112A patent/JP2003523475A/ja active Pending
- 2001-01-25 EP EP01912671A patent/EP1263902A1/en not_active Withdrawn
- 2001-01-25 WO PCT/US2001/002379 patent/WO2001055269A1/en not_active Application Discontinuation
- 2001-01-25 CA CA 2397969 patent/CA2397969A1/en not_active Abandoned
- 2001-01-25 BR BR0108110A patent/BR0108110A/pt not_active IP Right Cessation
- 2001-01-25 MX MXPA02007285A patent/MXPA02007285A/es not_active Application Discontinuation
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012516376A (ja) * | 2009-01-30 | 2012-07-19 | ザ・ボーイング・カンパニー | ハイブリッドコーティング及び関連の塗布方法 |
| JP2014505116A (ja) * | 2010-11-23 | 2014-02-27 | トランジションズ オプティカル， インコーポレイテッド | 硬化性フォトクロミック組成物およびそれから調製される光学物品 |
| WO2012141250A1 (ja) * | 2011-04-13 | 2012-10-18 | 株式会社トクヤマ | フォトクロミック組成物 |
| JP2016540239A (ja) * | 2013-10-11 | 2016-12-22 | トランジションズ オプティカル， インコーポレイテッド | 有機溶媒前処理およびフォトクロミックコーティングを使用するフォトクロミック光学物品を調製する方法 |
| US10281628B2 (en) | 2013-10-11 | 2019-05-07 | Transitions Optical, Inc. | Method of preparing a photochromic optical article using an organic solvent pretreatment and photochromic coating |
| WO2021172404A1 (ja) * | 2020-02-27 | 2021-09-02 | 株式会社トクヤマ | 光学物品用プライマー組成物、および積層体 |
Also Published As
| Publication number | Publication date |
|---|---|
| BR0108110A (pt) | 2003-03-25 |
| AU4142601A (en) | 2001-08-07 |
| EP1263902A1 (en) | 2002-12-11 |
| MXPA02007285A (es) | 2003-09-22 |
| WO2001055269A1 (en) | 2001-08-02 |
| CA2397969A1 (en) | 2001-08-02 |
| US20020009599A1 (en) | 2002-01-24 |
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